WO2017149457A1 - Compositions chimiquement résistantes de polycarbonate-polyester, procédés de fabrication et objets correspondants - Google Patents

Compositions chimiquement résistantes de polycarbonate-polyester, procédés de fabrication et objets correspondants Download PDF

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WO2017149457A1
WO2017149457A1 PCT/IB2017/051172 IB2017051172W WO2017149457A1 WO 2017149457 A1 WO2017149457 A1 WO 2017149457A1 IB 2017051172 W IB2017051172 W IB 2017051172W WO 2017149457 A1 WO2017149457 A1 WO 2017149457A1
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poly
composition
ethylene
measured
copolymer
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Yagang CHEN
Bing Guan
Lin Chen
Dake Shen
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SABIC Global Technologies BV
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SABIC Global Technologies BV
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Priority to EP17711337.0A priority Critical patent/EP3423527B1/fr
Priority to CN201780010158.9A priority patent/CN108699327B/zh
Priority to US16/079,883 priority patent/US10179854B1/en
Publication of WO2017149457A1 publication Critical patent/WO2017149457A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/201—Pre-melted polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D169/00—Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates
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    • C08J2369/00—Characterised by the use of polycarbonates; Derivatives of polycarbonates
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    • C08J2423/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2423/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2423/04—Homopolymers or copolymers of ethene
    • C08J2423/08—Copolymers of ethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2433/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2433/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2433/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2433/10—Homopolymers or copolymers of methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2467/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2471/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2483/10—Block- or graft-copolymers containing polysiloxane sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08L2203/12—Applications used for fibers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/14—Applications used for foams
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08L2203/16—Applications used for films
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend

Definitions

  • Polycarbonate compositions are widely used as engineering thermoplastics in a wide variety of applications due to their good heat resistance, impact resistance, and
  • the polycarbonate compositions can be subject to environmental stress cracking (ESC).
  • ESC environmental stress cracking
  • Attempts to improve the chemical resistance of the compositions have included the incorporation of thermoplastic polyesters or other polymers into the compositions.
  • chemical resistance of even these compositions does not meet more stringent requirements. It can further be difficult to obtain excellent chemical resistance while maintaining a good balance of processing and mechanical properties, for example flow and impact properties.
  • Polycarbonate compositions having improved chemical resistance, good flow, and good impact properties including specific amounts of a polycarbonate; a poly(l,4- cyclohexanedimethylene terephthalate); a poly(carbonate-siloxane); a thermoplastic poly(ester- ether) copolymer, preferably comprising poly(butylene terephthalate) blocks and poly(oxyCi-C 4 alkylene units); and an ethylene- alkyl acrylate copolymer, wherein alkyl is a Ci-C 4 straight chain, unsaturated hydrocarbon group; wherein the weight percentages are based on the total weight of the polymer composition are provided.
  • a polymer composition comprising: 15 to 60 weight percent (wt%), preferably 20 to 56 wt% of a polycarbonate; 30 to 60 wt%, preferably 28 to 50 wt% of a poly(l,4- cyclohexanedimethylene terephthalate); 0.05 to 35 wt%, preferably 0.1 to 30 wt% of a poly(carbonate-siloxane); 0.5 to 18 wt%, preferably 1 to 13 wt% of a thermoplastic poly(ester- ether) copolymer, preferably comprising poly(butylene terephthalate) blocks and poly(oxyCi-C 4 alkylene units); and 0.5 to 8 wt% of ethylene- alkyl (meth)acrylate copolymer, wherein alkyl is a Ci-C 4 straight chain, unsaturated hydrocarbon group; wherein the weight percentages are based on the total weight of the polymer composition is provided.
  • J/m Joules per meter
  • An article molded from the polymer composition having a melt volume rate of greater than 25, preferably greater than 28 cubic centimeters (cm 3 )/10 minutes, measured as per ASTM method D1238 at 300°C and 1.2 kilograms (kg); and a heat distortion temperature of 75 to 90°C, measured as per ASTM method D648 on a 3.2mm bar at 1.82 MegaPascals (MPa) is provided.
  • compositions and articles comprising the compositions are also described.
  • the polycarbonates used in the formulations include homopolycarbonates and copolycarbonates having repeating structural carbonate units of the formula (1)
  • R 1 groups wherein at least 60 percent of the total number of R 1 groups are aromatic, or each R 1 contains at least one C 6 -30 aromatic group.
  • Polycarbonates and their methods of manufacture are known in the art, being described, for example, in WO 2013/175448 Al, US 2014/0295363, and WO 2014/072923.
  • Polycarbonates and copolycarbonates are generally manufactured from bisphenol compounds such as 2,2-bis(4-hydroxyphenyl) propane (“bisphenol-A” or "BPA”), 3,3-bis(4- hydroxyphenyl) phthalimidine, l,l-bis(4-hydroxy-3-methylphenyl)cyclohexane, or l,l-bis(4- hydroxyphenyl)-3,3,5-trimethylcyclohexane (isophorone), or a combination comprising at least one of the foregoing bisphenol compounds can also be used.
  • bisphenol compounds such as 2,2-bis(4-hydroxyphenyl) propane (“bisphenol-A” or "BPA”), 3,3-bis(4- hydroxyphenyl) phthalimidine, l,l-bis(4-hydroxy-3-methylphenyl)cyclohexane, or l,l-bis(4- hydroxyphenyl)-3,3,5-trimethylcyclohexane (isophorone), or a combination compris
  • the polycarbonate is a homopolymer derived from BPA; or a copolycarbonate derived from BPA and another bisphenol or dihydroxy aromatic compound such as resorcinol. In a specific embodiment the polycarbonate is a BPA homopolycarbonate.
  • the polycarbonates can have an intrinsic viscosity, as determined in chloroform at 25°C, of 0.3 to 1.5 deciliters per gram (dl/gm), specifically 0.45 to 1.0 dl/gm.
  • the polycarbonates can have a weight average molecular weight of 10,000 to 200,000 grams per mole (g/mol), specifically 20,000 to 100,000 g/mol, specifically 15,000 to 30,000 g/mol as measured by gel permeation chromatography (GPC), using a crosslinked styrene-divinylbenzene column and calibrated to bisphenol A homopolycarbonate references.
  • GPC samples are prepared at a concentration of 1 milligram (mg) per milliliter (ml), and are eluted at a flow rate of 1.5 ml per minute.
  • the polycarbonate has flow properties useful for the manufacture of thin articles.
  • the polycarbonate can have a melt volume ratio (MVR) of 5 to 150 cubic centimeters (cc)/10 minute (min), specifically 7 to 125 cc/10 min, more specifically 9 to 110 cc/10 min, and still more specifically 10 to 100 cc/10 min, measured at 300°C and a load of 1.2 kilograms according to ASTM D1238-04.
  • MVR melt volume ratio
  • composition further includes a poly(l,4-cyclohexanedimethylene
  • the cyclohexane ring can be the cis-isomer, the trans-isomer, or a combination comprising at least one of the foregoing isomers.
  • the PCT can have an intrinsic viscosity, as determined in chloroform at 25°C, of 0.3 to 1.5 deciliters per gram
  • dl/gm specifically 0.45 to 1.0 dl/gm
  • a weight average molecular weight 10,000 to 200,000 Daltons, specifically 20,000 to 100,000 Daltons, as measured by gel permeation chromatography (GPC), using a crosslinked styrene-divinylbenzene column and calibrated to polystyrene standards.
  • a poly(carbonate-siloxane) copolymer is further present.
  • Poly(carbonate- siloxane)s comprise carbonate units of formula (1) as described above, and repeating
  • each R is independently a C1-C13 monovalent organic group.
  • R can be a C1-C13 alkyl, C1-C13 alkoxy, C2-C13 alkenyl, C2-C13 alkenyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C 6 -Ci 4 aryl, C 6 -Cio aryloxy, C7-C13 arylalkyl, C7-C13 aralkoxy, C7-C13 alkylaryl, or C7-C13 alkylaryloxy.
  • the foregoing groups can be fully or partially halogenated with fluorine, chlorine, bromine, or iodine, or a combination thereof. Combinations of the foregoing R groups can be used in the same copolymer.
  • E in formula (3) can vary widely depending on the type and relative amount of each component in the polycarbonate composition, the desired properties of the composition, and like considerations. Generally, E has an average value of 2 to 1,000, specifically 2 to 500, 2 to 200, or 2 to 125, 5 to 80, or 10 to 70. In an embodiment, E has an average value of 10 to 80 or 10 to 40, and in still another embodiment, E has an average value of 40 to 80, or 40 to 70. Where E is of a lower value, e.g., less than 40, it can be desirable to use a relatively larger amount of the poly(carbonate-siloxane) copolymer. Conversely, where E is of a higher value, e.g., greater than 40, a relatively lower amount of the poly(carbonate-siloxane) copolymer can be used.
  • R is methyl, or a combination of methyl and trifluoropropyl, or a combination of methyl and phenyl.
  • a combination of a first and a second (or more) poly(carbonate-siloxane) copolymers can be used, wherein the average value of E of the first copolymer is less than the average value of E of the second copolymer.
  • the polysiloxane blocks are of formula (11)
  • each R can be the same or different, and is as defined above; and Ar can be the same or different, and is a substituted or unsubstituted C6-C30 arylene, wherein the bonds are directly connected to an aromatic moiety.
  • Ar groups in formula (11) can be derived from a C6-C30 dihydroxy arylene compound, for example, l,l-bis(4-hydroxyphenyl) methane, l,l-bis(4-hydroxyphenyl) ethane, 2,2-bis(4-hydroxyphenyl) propane, 2,2-bis(4-hydroxyphenyl) butane, 2,2-bis(4-hydroxyphenyl) octane, l,l-bis(4-hydroxyphenyl) propane, l,l-bis(4- hydroxyphenyl) n-butane, 2,2-bis(4-hydroxy-l-methylphenyl) propane, l,l-bis(4- hydroxyphenyl) cyclohexane, bis(4-hydroxyphenyl sulfide), and l,l-bis(4-hydroxy-t- butylphenyl) propane.
  • Combinations comprising at least one of the foregoing dihydroxy compounds can also be used.
  • R and E are as described above, and each R 5 is independently a divalent C1-C30 organic group, and wherein the polymerized polysiloxane unit is the reaction residue of its
  • polysiloxane blocks are of formula 14):
  • R 6 in formula (14) is a divalent C 2 -C 8 aliphatic.
  • Each M in formula (14) can be the same or different, and can be a halogen, cyano, nitro, Ci-Cs alkylthio, Ci-Cs alkyl, Ci-Cs alkoxy, C 2 -Cs alkenyl, C 2 -Cs alkenyloxy, C3-C8 cycloalkyl, C3-C8 cycloalkoxy, C 6 -Cio aryl, C 6 -Cio aryloxy, C 7 -Ci 2 aralkyl, C 7 -Ci 2 aralkoxy, C 7 -Ci 2 alkylaryl, or C 7 -Ci 2 alkylaryloxy, wherein each n is independently 0, 1, 2, 3, or 4.
  • M is bromo or chloro, an alkyl such as methyl, ethyl, or propyl, an alkoxy such as methoxy, ethoxy, or propoxy, or an aryl such as phenyl, chlorophenyl, or tolyl;
  • R 6 is a dimethylene, trimethylene or tetramethylene; and
  • R is a Ci-Cs alkyl, haloalkyl such as trifluoropropyl, cyanoalkyl, or aryl such as phenyl, chlorophenyl or tolyl.
  • R is methyl, or a combination of methyl and trifluoropropyl, or a combination of methyl and phenyl.
  • R is methyl
  • M is methoxy
  • n is one
  • R 6 is a divalent C1-C3 aliphatic group.
  • the poly(carbonate-siloxane) copolymer can comprise 10 to 30 wt% of polysiloxane units.
  • Blocks of formula (3) can be derived from the corresponding dihydroxy polysiloxane, which in turn can be prepared effecting a platinum-catalyzed addition between the siloxane hydride and an aliphatically unsaturated monohydric phenol such as eugenol, 2-alkylphenol, 4-allyl-2-methylphenol, 4-allyl-2- phenylphenol, 4-allyl-2-bromophenol, 4-allyl-2-t-butoxyphenol, 4-phenyl-2-phenylphenol, 2- methyl-4-propylphenol, 2-allyl-4,6-dimethylphenol, 2-allyl-4-bromo-6-methylphenol, 2-allyl-6- methoxy-4-methylphenol and 2-allyl-4,6-dimethylphenol.
  • an aliphatically unsaturated monohydric phenol such as eugenol, 2-alkylphenol, 4-allyl-2-methylphenol, 4-allyl-2- phenylphenol, 4-allyl-2-bromophenol, 4-allyl-2
  • the poly(carbonate- siloxane) copolymers can then be manufactured, for example, by the synthetic procedure of European Patent Application Publication No. 0 524 731 Al of Hoover, page 5, Preparation 2.
  • the transparent copolymers can be manufactured using one or both of the tube reactor processes described in U.S. Patent Application No. 2004/0039145 A 1 or the process described in U.S. Patent No. 6,723,864 can be used to synthesize the poly(carbonate-siloxane) copolymers.
  • the poly(carbonate-siloxane) copolymers can comprise 50 to 99 weight percent of carbonate units and 1 to 50 weight percent siloxane units. Within this range, the
  • polyorganosiloxane-polycarbonate copolymer can comprise 70 to 98 weight percent, more specifically 75 to 97 weight percent of carbonate units and 2 to 30 weight percent, more specifically 3 to 25 weight percent siloxane units.
  • a poly(carbonate- siloxane) block copolymer of bisphenol A blocks and eugenol capped polydimethylsilioxane blocks, of the formula is used, wherein x is 1 to 200, specifically 5 to 85, specifically 10 to 70, specifically 15 to 65, and more specifically 40 to 60; x is 1 to 500, or 10 to 200, and z is 1 to 1000, or 10 to 800. In an embodiment, x is 1 to 200, y is 1 to 90 and z is 1 to 600, and in another embodiment, x is 30 to 50, y is 10 to 30 and z is 45 to 600.
  • the polysiloxane blocks can be randomly distributed or controlled distributed among the polycarbonate blocks.
  • the polycarbonate is a poly(carbonate-siloxane) copolymer comprising bisphenol A carbonate units and siloxane units, for example blocks containing 5 to 200 dimethylsiloxane units, such as those commercially available under the trade name EXL from SABIC.
  • the poly(carbonate- siloxane) copolymer can comprise 10 wt% or more, specifically 12 wt% or more, and more specifically 14 wt% or more, of the polysiloxane copolymer based on the total weight of the poly(carbonate-siloxane) copolymer.
  • Polyorganosiloxane-polycarbonates can have a weight average molecular weight of 2,000 to 100,000 Daltons, specifically 5,000 to 50,000 Daltons as measured by gel permeation chromatography using a crosslinked styrene-divinyl benzene column, at a sample concentration of 1 milligram per milliliter, and as calibrated with polycarbonate standards.
  • the polyorganosiloxane-polycarbonates can have a melt volume flow rate, measured at 300°C/1.2 kg, of 1 to 50 cubic centimeters per 10 minutes (cc/10 min), specifically 2 to 30 cc/10 min. Mixtures of polyorganosiloxane-polycarbonates of different flow properties can be used to achieve the overall desired flow property.
  • thermoplastic poly(ester-ether) copolymer also known in the art as thermoplastic elastomers or thermoplastic ester elastomers (TPEE) consist essentially of "soft block" long-chain ester units of formula (4)
  • G is a derived from a poly(Ci-C 4 alkylene oxide) glycol having a number- average molecular weight of 400 to 6000, and R 20 is derived from a C 4 -C 2 4 aliphatic or aromatic dicarboxylic acid, preferably an aromatic dicarboxylic acid; and "hard block" short-chain ester units of formula (5)
  • D is a Ci-Cio alkylene or cycloalkylene derived from the corresponding diol having a molecular weight of less than or equal to 300; and R 20 is derived from a C 4 -C 24 aliphatic, alicyclic, or aromatic dicarboxylic acid, preferably an aromatic dicarboxylic acid; with the proviso that the short-chain ester units constitute about 40% to about 90% by weight of the poly(ether-ester) block copolymer, and the long-chain ester units constitute about 10% to about 60% by weight of the poly(ether-ester) block copolymer.
  • the hard blocks are crystallizable materials that provide physical integrity, heat resistance, and chemical resistance, and the soft blocks provide elastomeric properties.
  • the melting point (Tm) of the hard block can be 120 to 200°C, or from 150 to 195°C
  • glass transition temperature (Tg) of the soft block can be -25 to -85°C, or from -45 to -65°C.
  • the hard block units of the poly(ether-ester) copolymers are derived from the reaction of a dicarboxylic acid component (which as used herein includes chemical equivalents thereof, for example acid chlorides) with a short chain Ci- Cio aliphatic or alicyclic diol component (which as used herein includes chemical equivalents thereof, for example methyl esters).
  • the hard block units of the poly(ether-ester) copolymer are derived from a C6-C24 aromatic dicarboxylic acid.
  • aromatic dicarboxylic acids include isophthalic acid, terephthalic acid, l,2-di(p-carboxyphenyl)ethane, 4,4'- dicarboxydiphenyl ether, and 4,4'-bisbenzoic acid. Acids containing fused rings can also be present, such as in 1,4-, 1,5-, or 2,6-naphthalenedicarboxylic acids.
  • Representative aromatic dicarboxylic acids include C 6 aromatic dicarboxylic acids.
  • isophthalic acid is present in an amount from 0 to 30 mole%, (e.g., 15 to 25 mole%), based on the total moles of isophthalic acid groups and terephthalic acid groups in the hard block units.
  • the aromatic hard block units comprise 70 to 100 mole% of terephthalic acid groups and 0 to 30 mole% of isophthalic acid groups.
  • the hard block units of the poly(ether-ester) copolymer are derived from a C6-C30 alicyclic dicarboxylic acid.
  • alicyclic dicarboxylic acids include the various isomers of 1,4-cyclohexane dicarboxylic acid (cis, trans, or a combination thereof), 1,4-cyclohexane dicarboxylic acid (cis, trans, or a combination thereof), 1,3- cyclohexane dicarboxylic acid (cis, trans, or a combination thereof), 1,2-cyclohexane dicarboxylic acid (cis, trans, or a combination thereof), and the various isomers of decalin dicarboxylic acid, norbornane dicarboxylic acid, adamantane dicarboxylic acid, and
  • the short chain C1-C10 diol component can comprise, for example, ethylene glycol, diethylene glycol, trimethylene glycol, 1,3-propane diol, 1,4-butane diol, or a
  • the short chain C1-C10 diol component comprises, in addition to 1,4-butanediol, diethylene glycol and ethylene glycol monomers that are added during the polymerization.
  • the amount of such monomers can vary, depending on the application.
  • the diethylene glycol groups and ethylene glycol groups can be present in an amount of more than 0 to 5 wt% ethylene glycol and more than 0 to 5 wt% diethylene glycol.
  • diethylene glycol is present in an amount from 0.02 to 2 wt%, based on the weight of the hard blocks.
  • Specific hard block units comprise, consist essentially of, or consist of ester units containing 1,4-butane diol groups, together with 70 to 100 mole% of terephthalic acid groups and 0 to 30 mole% of isophthalic acid groups, based on the total moles of hard block ester units.
  • the soft block units are formed by the reaction of a dicarboxylic acid component (which as used herein includes chemical equivalents thereof, for example acid chlorides) with a poly(oxyalkylene) diol component (which as used herein includes chemical equivalents thereof, for example methyl esters).
  • the dicarboxylic acid component used to manufacture the soft block units comprises one or more dicarboxylic acids.
  • the dicarboxylic acids contain a C2-C30 alkylene group, a C6-C30 alicyclic group, a C6-C30 alkyl aromatic group, or a C6-C30 aromatic group.
  • aromatic dicarboxylic acids include isophthalic acid, terephthalic acid, l,2-di(p-carboxyphenyl)ethane, 4,4'-dicarboxydiphenyl ether, and 4,4'- bisbenzoic acid.
  • Acids containing fused rings can also be present, such as in 1,4-, 1,5-, or 2,6- naphthalenedicarboxylic acids.
  • Representative dicarboxylic acids include terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, and cyclohexane dicarboxylic acid.
  • Terephthalic acid can be used alone, or in combination with isophthalic acid.
  • the poly(oxyalkylene) diol is a poly(Ci-C 4 alkylene oxide) glycol having a number average molecular weight of 400 to 6000 Daltons, for example poly(oxytetramethylene) glycol (PTHF) derived from tetrahydrofuran.
  • PTHF poly(oxytetramethylene) glycol
  • the poly(ether-ester) copolymers can comprise from 10 to 73 wt%, from 20 to 65 wt%, or from 40 to 60 wt%), of PTHF groups, based on the weight of the copolymer.
  • the PTHF groups have a molecular weight of 300 to 1800 Daltons; in certain embodiments, the poly(oxytetramethylene) glycol groups have a molecular weight from 700 to 1700 Daltons or from 900 to 1600 Daltons.
  • poly(ether-ester) copolymers are commercially available, for example under the trademarks ARNITEL EM400 and ARNITEL EL630 poly(ether-ester) copolymers from DSM; HYTREL 3078, HYTREL 4056, HYTREL 4556, and HYTREL 6356 poly(ether-ester) copolymers from DuPont; and ECDEL 9966 poly(ether-ester) copolymer from Eastman Chemical.
  • the soft block is derived from tetrahydrofuran.
  • the hard block is based on poly(butylene terephthalate) (PBT).
  • PBT poly(butylene terephthalate)
  • the hard block contains isophthalate units in addition to terephthalate units.
  • the hard block is based on poly(l,4-cyclohexane- dimethanol-l,4-cyclohexane dicarboxylate) (PCCD) units.
  • the ethylene- alkyl (meth)acrylate copolymer comprises units derived from ethylene and from a straight chain (Ci-C 4 ) alkyl (meth)acrylate, i.e., an acrylate or methacrylate.
  • the ethylene- alkyl (meth)acrylate copolymer can be an ethylene-methyl acrylate copolymer or ethylene-ethyl acrylate copolymer, or a combination comprising at least one of the foregoing.
  • the ethylene-methyl acrylate copolymer or ethylene-ethyl acrylate copolymer can have an acrylate content of 15 to 30 wt%, preferably 18 to 28 wt%.
  • the polycarbonate compositions can further comprise an additive composition comprising one or more additives selected to achieve a desired property, with the proviso that each additive is also selected so as to not significantly adversely affect a desired property of the polycarbonate composition.
  • the additive composition or individual additives can be mixed at a suitable time during the mixing of the components for forming the composition.
  • the additive can be soluble or non-soluble in polycarbonate.
  • the additive composition can include a filler (e.g., a particulate polytetrafluoroethylene (PTFE), glass, carbon, mineral, or metal), an antioxidant, a thermal stabilizer, a quencher, a colorant (e.g, a dye or pigment), a mold release agent, a light stabilizer, an ultraviolet light absorber, a plasticizer, a lubricant, an antistatic agent, a flame retardant, an anti-drip agent (e.g., a PTFE-encapsulated styrene-acrylonitrile copolymer (TSAN)), or a combination comprising one or more of the foregoing.
  • a filler e.g., a particulate polytetrafluoroethylene (PTFE), glass, carbon, mineral, or metal
  • an antioxidant e.g., a thermal stabilizer, a quencher, a colorant (e.g, a dye or pigment), a mold release agent, a light stabilizer,
  • the additives are used in the amounts generally known to be effective.
  • the total amount of the additive composition can be 0.001 to 10.0 wt%, or 0.01 to 5 wt%, or 0.001 to 0.5 wt%, or 0.005 to 0.1 wt% each based on the total weight of the polymer in the composition.
  • the additive composition comprises a quencher, a mold release agent, and one or more antioxidants.
  • the polycarbonate compositions can be manufactured by various methods known in the art. For example, powdered polycarbonate, and other optional components are first blended, optionally with any fillers, in a high speed mixer or by hand mixing. The blend is then fed into the throat of a twin-screw extruder via a hopper. Alternatively, at least one of the components can be incorporated into the composition by feeding it directly into the extruder at the throat or downstream through a sidestuffer, or by being compounded into a masterbatch with a desired polymer and fed into the extruder. The extruder is generally operated at a temperature higher than that necessary to cause the composition to flow. The extrudate can be immediately quenched in a water bath and pelletized. The pellets so prepared can be one-fourth inch long or less as desired. Such pellets can be used for subsequent molding, shaping, or forming
  • an article molded from the polymer composition can have a notched Izod impact strength greater than or equal to 650 J/m, preferably greater than or equal to 700 J/m, more preferably greater than or equal to 710 J/m measured as per ASTM method D256 on a 3.2 millimeter (mm) thick sample.
  • An article molded from the polymer composition can have a resistance to break of at least 4 days, preferably at least 5 days, measured as per ASTM D638 method at 50 mm/min after exposure to sunscreen under 1% strain at 23 °C.
  • An article molded from the polymer composition can have a melt volume rate of greater than 25, preferably greater than 28 cm3/10 minutes, measured as per ASTM method D1238 at 300°C and 1.2 kilograms.
  • An article molded from the polymer composition can have a heat distortion temperature of 75 to 90°C, measured as per ASTM method D648 on a 3.2 mm bar at 1.82MPa.
  • Sample preparation and testing After drying the obtained pellets at 100°C for 4 hours, all the testing specimens in accordance with ASTM standards were prepared from the pellets using a 150 T injection molding machine at a melt temperature 295°C and at a mold temperature of 75°C (see Table 3 for parameters used).
  • Table 5 shows the compositions (wt%) and properties of the various examples and comparative examples.
  • each composition was formulated with 0.01 wt% H3PO3 quencher, 0.15 wt% Antioxidant-2, and 0.12 wt% of Antioxidant- 1. Any total of the components for each composition that does not equal 100% is due to rounding of the amounts.
  • Embodiment 1 A polymer composition comprising: 15 to 60 wt%, preferably 20 to 56 wt% of a polycarbonate; 30 to 60 wt%, preferably 28 to 50 wt% of a poly(l,4- cyclohexanedimethylene terephthalate); 0.05 to 35 wt%, preferably 0.1 to 30 wt% of a poly(carbonate-siloxane); 0.5 to 18 wt%, preferably 1 to 13 wt% of a thermoplastic poly(ester- ether) copolymer, preferably comprising poly(butylene terephthalate) blocks and poly(oxyCi-C 4 alkylene units); and 0.5 to 8 wt% of ethylene- alkyl (meth)acrylate copolymer, wherein alkyl is a Ci-C 4 straight chain, unsaturated hydrocarbon group; wherein the weight percentages are based on the total weight of the polymer composition.
  • Embodiment 2 The composition of embodiment 1, wherein an article molded from the polymer composition has a notched Izod impact strength greater than or equal to 650 J/m, preferably greater than or equal to 700 J/m, more preferably greater than or equal to 710 J/m measured as per ASTM method D256 on a 3.2 millimeter (mm) thick sample; and a resistance to break of at least 4 days, preferably at least 5 days, measured as per ASTM D638 method at 50 mm/min after exposure to sunscreen under 1% strain at 23 °C.
  • Embodiment 3 The composition of embodiments 1 or 2, wherein an article molded from the polymer composition has a melt volume rate of greater than 25, preferably greater than 28 cm 3 /10 minutes, measured as per ASTM method D1238 at 300°C and 1.2 kilograms; and a heat distortion temperature of 75 to 90°C, measured as per ASTM method D648 on a 3.2mm bar at 1.82MPa.
  • Embodiment 4 The composition of any one or more of embodiments 1 to 3, wherein the ethylene- alkyl (meth)acrylate copolymer is ethylene-methyl acrylate copolymer or ethylene-ethyl acrylate copolymer, or a combination comprising at least one of the foregoing.
  • Embodiment 5 The composition of embodiment 4, wherein the ethylene-methyl acrylate copolymer or ethylene-ethyl acrylate copolymer has an acrylate content of 15 to 30 wt%, preferably 18 to 28 wt%.
  • Embodiment 6 The composition of any one or more of embodiments 1 to 5, wherein the thermoplastic poly(ester-ether) copolymer comprises 40 to 90 wt%, preferably 25 to 75 wt% of a hard block comprising polybutylene terephthalate repeating units having an average molecular weight less than 250 g/mol and 60 to 90 wt%, preferably 75 to 25 wt% of
  • polyoxyalkylene units having a number average molecular weight less of 400 to 6000 g/mole.
  • Embodiment 7 The composition of any one or more of embodiments 1 to 6, wherein the polycarbonate is a bisphenol-A polycarbonate having a weight average molecular weight between 15,000 and 30,000 g/mol.
  • Embodiment 8 The composition of any one or more of embodiments 1 to 7, wherein the poly(carbonate-siloxane) copolymer comprises 10 to 30 wt% of polysiloxane units.
  • Embodiment 9 The composition of any one or more of embodiments 1 to 8, wherein the poly(carbonate-siloxane) copolymer comprises the formula: wherein x is 1 to 200, y is 1 to 90 and z is 1 to 600.
  • Embodiment 10 The composition of any one or more of embodiments 1 to 9, further comprising a filler, an antioxidant, a thermal stabilizer, a quencher, a colorant, a mold release agent, a light stabilizer, an ultraviolet light absorber, a plasticizer, a lubricant, an antistatic agent, a flame retardant, an anti-drip agent, or a combination comprising at least one of the foregoing.
  • Embodiment 11 The composition of any one or more of embodiments 1 to 10, comprising 32 to 47 wt% polycarbonate, preferably a bisphenol A homopolycarbonate;
  • polyester preferably poly(l,4-cyclohexanedimethylene terephthalate); 10 to 25 wt% oly(carbonate-siloxane), preferably of the formula
  • Embodiment 12 A method of preparing a polymer composition, comprising: melt blending the components of the polymer composition of embodiment 1.
  • Embodiment 13 An article comprising the polymer composition of any of embodiments 1 to 11.
  • Embodiment 14 The article of claim 13, wherein the article is a sheet, a film, a multilayer sheet, a multilayer film, a molded part, an extruded profile, a fiber, a coated part, or a foam.
  • Embodiment 15 The article of embodiment 13 or 14, having a notched Izod impact strength greater than or equal to 650 J/m, preferably greater than or equal to 700 J/m, more preferably greater than or equal to 710 J/m measured as per ASTM method D256 on a 3.2 millimeter (mm) thick sample; and a resistance to break of at least 4 days, preferably at least 5 days, measured as per ASTM D638 method at 50 mm/min after exposure to sunscreen under 1% strain at 23 °C.
  • Embodiment 16 The article of any one or more of embodiments 13 to 15, having a melt volume rate of greater than 25, preferably greater than 28 cm 3 /10 minutes, measured as per ASTM method D1238 at 300°C and 1.2 kilograms; and a heat distortion temperature of between 75-90°C, measured as per ASTM method D648 on a 3.2 mm bar at 1.82MPa.
  • the invention may alternatively comprise, consist of, or consist essentially of, any appropriate components herein disclosed.
  • the invention may additionally, or alternatively, be formulated so as to be devoid, or substantially free, of any components, materials, ingredients, adjuvants or species used in the prior art compositions or that are otherwise not necessary to the achievement of the function and/or objectives of the present invention.
  • alkyl includes branched or straight chain, unsaturated aliphatic C1-C30 hydrocarbon groups e.g., methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, s- pentyl, n- and s-hexyl, n-and s-heptyl, and, n- and s-octyl.
  • Alkenyl means a straight or branched chain, monovalent hydrocarbon group having at least one carbon-carbon double bond
  • alkenyloxy means an alkenyl group that is linked via an oxygen
  • Alkoxy means an alkyl group that is linked via an oxygen (i.e., alkyl-O-), for example methoxy, ethoxy, and sec-butyloxy groups.
  • Alkylene means a straight or branched chain, saturated, divalent aliphatic hydrocarbon group (e.g., methylene (-CH 2 -) or propylene (-(CH 2 ) 3 -)).
  • Cycloalkyl means a non-aromatic monovalent monocyclic or multicylic hydrocarbon group having at least three carbon atoms.
  • Cycloalkoxy means a cycloalkyl group that is linked via an oxygen (i.e., cycloalkyl-O-).
  • Aryl means an aromatic monovalent group containing only carbon in the aromatic ring or rings.
  • Arylene refers to an aromatic divalent group containing only carbon in the aromatic ring or rings.
  • alkyloxy means an aryl group as defined above with the indicated number of carbon atoms attached through an oxygen bridge (-0-).
  • alkylaryloxy means an aryloxy group as defined above, where the aryl group is substituted with an alkyl group.
  • alkylaryl means an aryl group as defined above, where the aryl group is substituted with an alkyl group.
  • Arylalkyl or
  • aralkyl means an alkyl group that has been substituted with an aryl group, with benzyl being an exemplary arylalkyl group.
  • Cycloalkylene means a divalent cyclic alkylene group, -C n H 2n - x , wherein x is the number of hydrogens replaced by cyclization(s).
  • halo means a group or compound including one more of a fluoro, chloro, bromo, iodo, and astatino substituent. A combination of different halo groups (e.g., bromo and fluoro) can be present. In an embodiment only chloro groups are present.
  • hetero means that the compound or group includes at least one ring member that is a heteroatom (e.g., 1, 2, or 3 heteroatom(s)), wherein the heteroatom(s) is each independently N, O, S, or P.
  • substituted means that the compound or group is substituted with at least one (e.g., 1, 2, 3, or 4) substituents independently selected from a C1-C9 alkoxy, a
  • C12 cycloalkyl a C2-C12 alkenyl, a C5-C12 cycloalkenyl, a C6-C12 aryl, a C 7 -Ci 3 arylalkylene, a

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Abstract

L'invention concerne une composition de polymère, comprenant 15 et 60 % en poids, de préférence de 20 à 56 % en poids, d'un polycarbonate ; 30 à 60 % en poids, de préférence 28 à 50 % en poids d'un poly(téréphtalate de 1,4-cyclohexanediméthylène) ; 0,05 à 35 % en poids, de préférence 0,1 à 30 % en poids, d'un poly(carbonate-siloxane) ; 0,5 à 18 % en poids, de préférence 1 à 13 % en poids, d'un copolymère thermoplastique de poly(ester-éther), comprenant de préférence des blocs de poly(téréphtalate de butylène) et des motifs de poly(oxy-C1-C4-alkylène) ; et 0,5 à 8 % en poids de copolymère d'éthylène-(méth)acrylate d'alkyle, alkyle étant un groupe hydrocarboné, insaturé à chaîne linéaire en C1-C4 ; les pourcentages en poids étant basés sur le poids total de la composition de polymère. Un procédé de fabrication d'un objet comprenant les étapes de mélange, à l'état fondu, des constituants de la composition de polycarbonate est décrit. Un objet préparé par le procédé est également décrit.
PCT/IB2017/051172 2016-02-29 2017-02-28 Compositions chimiquement résistantes de polycarbonate-polyester, procédés de fabrication et objets correspondants Ceased WO2017149457A1 (fr)

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